ethyl 5-benzyloxy-6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-(E,5R)-2-hexenoate

Base Information

Chemical Name:ethyl 5-benzyloxy-6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-(E,5R)-2-hexenoate
CAS No.:866823-61-2
Molecular Formula:C₂₀H₂₈O₅
Molecular Weight:348.439
Hs Code.:

Synonyms:ethyl 5-benzyloxy-6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-(E,5R)-2-hexenoate

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Chemical Property of ethyl 5-benzyloxy-6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-(E,5R)-2-hexenoate

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Technology Process of ethyl 5-benzyloxy-6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-(E,5R)-2-hexenoate

There total 7 articles about ethyl 5-benzyloxy-6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-(E,5R)-2-hexenoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

: 889881-73-6
(S)-3-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 866823-61-2
ethyl 5-benzyloxy-6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-(E,5R)-2-hexenoate

Guidance literature:: In benzene; at 20 ℃; for 12h;
DOI:10.1016/j.tetasy.2005.07.001

Reference yield:

: 866823-59-8
(2R,4S)-5-hexene-1,2,4-triol

: 866823-61-2
ethyl 5-benzyloxy-6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-(E,5R)-2-hexenoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 76 percent / p-toluenesulfonic acid / 3 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

2.2: 96 percent / tetrahydrofuran / 8 h / Heating

3.1: BH₃*DMS / tetrahydrofuran / 8 h / 20 °C

3.2: 80 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

4.1: IBX / dimethylsulfoxide; tetrahydrofuran / 3 h / 20 °C

5.1: 89 percent / benzene / 12 h / 20 °C

With dimethylsulfide borane complex; sodium hydride; toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; benzene; 5.1: Wittig olefination;
DOI:10.1016/j.tetasy.2005.07.001

Reference yield:

: 117064-89-8
1-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-(2S)-3-buten-2-ol

: 866823-61-2
ethyl 5-benzyloxy-6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-(E,5R)-2-hexenoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 96 percent / tetrahydrofuran / 8 h / Heating

2.1: BH₃*DMS / tetrahydrofuran / 8 h / 20 °C

2.2: 80 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

3.1: IBX / dimethylsulfoxide; tetrahydrofuran / 3 h / 20 °C

4.1: 89 percent / benzene / 12 h / 20 °C

With dimethylsulfide borane complex; sodium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; benzene; 4.1: Wittig olefination;
DOI:10.1016/j.tetasy.2005.07.001